N-bromobutanimide → Methyl 4-(bromomethyl)-3-fluorobenzoate

HRID 2395012Notes

Reaction equation

HRID 2395012 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.[W].CC(N=NC(C#N)(C)C)(C#N)C>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][Br:13])[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 18973767Methyl 3-fluoro-4-methylbenzoate

Product 1

HCID 18766370Methyl 4-(bromomethyl)-3-fluorobenzoateYield 80%

Reagents, catalysts & solvents 3

HCID 6547AzobisisobutyronitrileCatalystHCID 23964TungstenCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of methyl 3-fluoro-4-methylbenzoate (4.3 g), N-bromosuccinimide (4.5 g) and AIBN (20 mg) in carbon tetrachloride was irradiated with a 100 W Tungsten lamp at reflux for 1 hour. The mixture was filtered through diatomaceous earth, and evaporated to give methyl 3-fluoro-4-(bromomethyl)benzoate (5.0 g).

Workup

  1. temperatureat reflux for 1 hour
  2. filtrationThe mixture was filtered through diatomaceous earth
  3. customevaporated

Sources & evidence

ORD record
ord-2b4f5d38e757485d95a4b80e85e61197
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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